Hydrochloric Acid → 1-(2-isopropylaminopropyl)-9-methoxy-3-methyl-3,4,5,5a,6,7-hexahydro-2H-naphth[1,2-d]azepine dihydrochloride

HRID 46517Notes

Reaction equation

HRID 46517 reaction equation
[ClH:1].O=[C:3]([CH3:23])[CH2:4][C:5]1[CH2:6][N:7]([CH3:22])[CH2:8][CH2:9][CH:10]2[CH2:19][CH2:18][C:17]3[C:12](=[CH:13][CH:14]=[C:15]([O:20][CH3:21])[CH:16]=3)[C:11]=12.[CH:24]([NH2:27])([CH3:26])[CH3:25].Cl.C([BH3-])#N.[Na+]>CO>[ClH:1].[ClH:1].[CH:24]([NH:27][CH:3]([CH3:23])[CH2:4][C:5]1[CH2:6][N:7]([CH3:22])[CH2:8][CH2:9][CH:10]2[CH2:19][CH2:18][C:17]3[C:12](=[CH:13][CH:14]=[C:15]([O:20][CH3:21])[CH:16]=3)[C:11]=12)([CH3:26])[CH3:25]

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 6363IsopropylamineHCID 5003444Sodium cyanoborohydride2×HCID 205555981-(2-oxopropyl)-9-methoxy-3-methyl-3,4,5,5a,6,7-hexahydro-2H-naphth[1,2-d]azepine hydrochloride

Product 1

HCID 205556111-(2-isopropylaminopropyl)-9-methoxy-3-methyl-3,4,5,5a,6,7-hexahydro-2H-naphth[1,2-d]azepine dihydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The solution of 0.84 g of 1-(2-oxopropyl)-9-methoxy-3-methyl-3,4,5,5a,6,7-hexahydro-2H-naphth[1,2-d]azepine hydrochloride, 1.28 ml of isopropylamine, 0.66 ml of 4.4 N methanolic hydrochloric acid and 0.17 g of sodium cyanoborohydride in 13 ml of methanol is refluxed overnight. Additional 0.085 g of sodium cyanoborohydride are added and the whole is again refluxed for 5 hours. The mixture is cooled, acidified to pH=1 with concentrated hydrochloric acid and the methanol evaporated. The aqueous solution is washed with diethyl ether, rendered basic to pH=10-11 with 3 N aqueous sodium hydroxide and extracted with diethyl ether. The ether extract is evaporated, the residue dissolved in acetone and 0.4 ml of 8 N ethanolic hydrochloric acid are added, to yield the 1-(2-isopropylaminopropyl)-9-methoxy-3-methyl-3,4,5,5 a,6,7-hexahydro-2H-naphth[1,2-d]azepine dihydrochloride melting at 257°-260° with decomposition.

Workup

  1. temperaturethe whole is again refluxed for 5 hours
  2. temperatureThe mixture is cooled
  3. customthe methanol evaporated
  4. washThe aqueous solution is washed with diethyl ether
  5. extractionextracted with diethyl ether
  6. extractionThe ether extract
  7. customis evaporated
  8. dissolutionthe residue dissolved in acetone
  9. addition0.4 ml of 8 N ethanolic hydrochloric acid are added

Sources & evidence

ORD record
ord-b5c80b41de4f40d6be6b7fa7e5497b71
Source dataset
uspto-grants-1979_11
Patent number
US04173633

Reaction notes

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